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Titolo:
Cation binding effect on hydrogen bonding in the complexes of lidocaine, tocainide and mexiletine with the acetate
Autore:
Remko, M; Rode, BM;
Indirizzi:
Comenius Univ, Dept Pharmaceut Chem, SK-83232 Bratislava, Slovakia Comenius Univ Bratislava Slovakia SK-83232 SK-83232 Bratislava, Slovakia Innsbruck Univ, Inst Gen Inorgan & Theoret Chem, Theoret Chem Div, A-6020 Innsbruck, Austria Innsbruck Univ Innsbruck Austria A-6020 m Div, A-6020 Innsbruck, Austria
Titolo Testata:
THEOCHEM-JOURNAL OF MOLECULAR STRUCTURE
, volume: 488, anno: 1999,
pagine: 135 - 139
SICI:
0166-1280(19991001)488:<135:CBEOHB>2.0.ZU;2-W
Fonte:
ISI
Lingua:
ENG
Soggetto:
ANTIARRHYTHMIC DRUGS; ION CHANNELS; HYDROCHLORIDE; MEMBRANES; ABINITIO;
Keywords:
lidocaine; mexiletine; torainide; antiarrhythmic-receptor interaction; cation binding effect; ab initio calculations;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
27
Recensione:
Indirizzi per estratti:
Indirizzo: Remko, M Comenius Univ, Dept Pharmaceut Chem, Odbojarov 10, SK-83232 Bratislava, Slovakia Comenius Univ Odbojarov 10 Bratislava Slovakia SK-83232 Slovakia
Citazione:
M. Remko e B.M. Rode, "Cation binding effect on hydrogen bonding in the complexes of lidocaine, tocainide and mexiletine with the acetate", THEOCHEM, 488, 1999, pp. 135-139

Abstract

The effect of binding of cations (Na+, K+) on the geometry and strength ofthe complexes pairing protonated antiarrhythmics lidocaine NH+, tocainide NH+, and mexiletine NH+ with the anionic acetate group forming charged NH+...O- bonds was studied using the ab initio SCF 3-21G level of theory. The coordination of the ions Na+ and K+ to the protonated antiar rhythmic-acetate systems considerably reduces the strength of the O-...+HN hydrogen bond. Of the two cations studied Na+ produces a larger destabilizing effect. The possible proton transfer from the drug towards the carboxylate anionic sitewas investigated in the case of the mexiletine NH+...-OCOCH3 complex. For both the isolated and the metal ion coordinated systems two-minima potentials at R-O...(N) = 2.75 Angstrom were found. The most stable minimum for theisolated system mexiletine NH+...-OCOCH3 corresponds to the neutral N...H-O hydrogen bond, in coordinated systems the presence of the cations Na+ andK+ in the vicinity of hydrogen bond considerably stabilize proton transferstructures. The most stable minimum in the coordinated systems correspond to charged O-...+HN complexes. (C) 1999 Elsevier Science B.V. All rights reserved.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 02/04/20 alle ore 01:57:47